Episode Summary

Alex Feldman is the founder of Tiger and Bear, an M&A advisory focused on tech and services businesses. Before that, he was Chief Strategy Officer and General Counsel at Amaysim, where he ran three acquisitions simultaneously during full lockdown in 2020 and 2021 to build a dominant player that was ultimately sold.

In this episode, Cheryl and Maxine unpack how to buy and sell businesses when the world is doing crazy stuff around you. Alex breaks down why today's volatility isn't actually that different from the GFC or COVID, why timing is the single most important variable in any deal, and what the SaaSpocalypse means for tech companies thinking about selling when their natural buyers are struggling.

You'll also hear why more than half of Tiger and Bear's recent deals involved European and Asian capital rather than American, why profitable venture-backed businesses are suddenly more attractive to strategics, and what happens when the IPO market disappears as an exit path. For founders who can't raise their next round, he offers blunt advice: never waste a crisis, cut costs to buy yourself runway, and remember that raising and selling are the same activity, you're just selling different amounts of shares.

Alex closes with his Big Cojones moment: putting every spare $500 into the stock market during the GFC with no idea where the bottom was, buying Macquarie Bank shares at $30 and riding them back up.

Time Stamps

00:00 - Intro

02:25 – Alex's first investment: going all in on the BHP Rio Tinto merger that never happened

06:19 – How to do M&A in volatile markets and why this cycle isn't that different

11:50 – Timing for buyers vs sellers: why uncertainty kills deals, not direction

13:08 – The SaaSpocalypse: what happens when your natural buyer is struggling

18:10 – Why European and Asian capital is replacing American buyers in Australia

21:08 – What M&A looks like in the Australian tech ecosystem right now

24:01 – When is a company big enough to buy and too small to be acquired

28:30 – Mergers of equals: why similar-sized companies come together in downturns

38:39 – How to become a disciplined buyer: capital, internal muscle, and integration

43:08 – Why the hardest part of any deal is admitting the other side does it better

47:54 – What to do when you can't raise: never waste a crisis

55:01 – Big Cojones moment: investing every spare dollar during the GFC

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